A calm lake with a buoy in the center, surrounded by a dense forest and a misty shoreline.

Waldoboro Vacation Rentals

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Our top choices for Waldoboro vacation rentals

1. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"It was a wonderful stay at this home. The home was incredibly clean, the beds were very comfortable and had great bedding on them. It was a great location to all the nearby places we wanted to go to. Loved the historic charm. We would love to come and stay again!"
United States
Tina S.
The price is CA $189
CA $690 total
includes taxes & fees
Sep 9 - Sep 10
Near Lakes, Bay & Trails! Historic Waldoboro Gem

2. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
The price is CA $249
CA $675 total
includes taxes & fees
Sep 9 - Sep 10
Near Lakes, Bay & Trails! Historic Waldoboro Gem

3. The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
The price is CA $1,218
CA $1,780 total
includes taxes & fees
Sep 7 - Sep 8
The Entire Waldoboro Inn

4. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (463 reviews)
"Great stay, great location."
United States
Jerold
The price is CA $178
CA $194 total
includes taxes & fees
Aug 23 - Aug 24
Trade Winds on the Bay

5. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (21 reviews)
"Great location for visiting the coast."
United States
Sallie S.
The price is CA $136
CA $550 total
includes taxes & fees
Aug 25 - Aug 26
Rustic Retreat Across from Lake; Family Friendly!

6. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (46 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
The price is CA $308
CA $554 total
includes taxes & fees
Aug 25 - Aug 26
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

7. ComfyDome Hill-Side Glamping

ComfyDome Hill-Side Glamping
Jefferson
10.0 out of 10, Exceptional, (6 reviews)
"Fun experience!"
United States
Fred R.
ComfyDome Hill-Side Glamping

8. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
The price is CA $182
CA $537 total
includes taxes & fees
Sep 3 - Sep 4
Rustic Retreat Across From Lake; Family Friendly!

9. ComfyDome Pond-Side Glamping

ComfyDome Pond-Side Glamping
Jefferson
10.0 out of 10, Exceptional, (6 reviews)
"My partner and I loved our stay here. It was very peaceful and the land was beautiful. We are looking forward to another trip in the future! "
United States
Kari S.
ComfyDome Pond-Side Glamping

10. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.4 out of 10, Very good, (12 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is CA $275
CA $388 total
includes taxes & fees
Aug 25 - Aug 26
Dome 3 at Come Spring Farm Glamping - Alpaca Farm

11. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
8.8 out of 10, Excellent, (10 reviews)
"Host was fast in responding to all questions and concerns. Location was good for being close to all shopping and eating. "
United States
Kim W.
The price is CA $200
CA $375 total
includes taxes & fees
Sep 1 - Sep 2
Bright 2-Bedroom Apartment Near Downtown Thomaston

12. Quiet & Lovely Lakefront Cottage for Families!

Quiet & Lovely Lakefront Cottage for Families!
Union
9.8 out of 10, Exceptional, (16 reviews)
"Evocative of my youth and going to the family lake camp in the summer. We had great weather and a great time. The cabin is a ‘Mainer’s’ memories wrapped in eclectic reminders. What a joy!"
United States
Venise B.
The price is CA $189
CA $706 total
includes taxes & fees
Sep 1 - Sep 2
Quiet & Lovely Lakefront Cottage for Families!

13. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (31 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is CA $149
CA $225 total
includes taxes & fees
Sep 15 - Sep 16
Simplicity-Just what you need! STR24-20

14. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (8 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
The price is CA $220
CA $270 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful Intown Studio ~ Walk to Shops & Dining

15. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (37 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is CA $235
CA $451 total
includes taxes & fees
Sep 15 - Sep 16
Peaceful, Centrally Located Home with Seasonal River Views

16. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (51 reviews)
"We enjoyed staying at this site but we had difficulty with the address. I would recommend putting the number 67 on the outside of the mud room door, which would make it much easier to find the location A member of our party had difficulty sleeping on the pull out couch and recommended a thicker mattress. We also smelled cigarettes upon entry into the building but once the door was open for a short time the smell went away. I would definitely stay at this site again when I the area."
United States
April
The price is CA $213
CA $421 total
includes taxes & fees
Sep 22 - Sep 23
2 Bedroom Close to Town Home

17. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is CA $125
CA $291 total
includes taxes & fees
Sep 15 - Sep 16
Happy Cottage Near Everything 11

18. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $165
CA $355 total
includes taxes & fees
Aug 25 - Aug 26
Cheerful Cottage with Loft 9

19. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is CA $178
CA $366 total
includes taxes & fees
Sep 15 - Sep 16
Spacious 1 Bedroom Cottage Close to Everything 5

20. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (38 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
The price is CA $298
CA $624 total
includes taxes & fees
Aug 31 - Sep 1
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waldoboro Hotel Reviews

Find out more about Waldoboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Waldoboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Waldoboro?

Yes, there are vacation rentals in Waldoboro close to Morse's Sauerkraut, or you can go with a secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the gardens in Waldoboro. Make sure you have time to check out the local tours and bars during your trip.

What are some of the best vacation home rentals that Waldoboro has to offer?

Comfortable, Close to Town Home, with Oceanview.: This vacation home rental outside Waldoboro offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Waldoboro?

With 21 Expedia vacation rentals, you're sure to find just the right place for your Waldoboro stay.

What’s there to see and do in Waldoboro?

Pemaquid Pond and Duckpuddle Pond are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Morse's Sauerkraut. In the larger area, you’ll find Fawcett's Antique Toy and Art Museum and St. George River.

What’s a vacation rental in Waldoboro like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Waldoboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family trip or a small group gathering.